Days 1–5: Cape Town (5 Nights)

Day 1 - Sep 6: Arrival & Waterfront Ease

Arrive in Cape Town and check into the hotel. After check-in, spend the afternoon/evening exploring the Cape Town Waterfront, an energetic mix of ocean views, design-forward shops, and excellent casual dining. It’s the ideal, low-effort introduction to the city after a long journey.

Day 2 - Sep 7: Table Mountain, Bo-Kaap & A Layered Evening

Begin the day with a cableway ride up Table Mountain, one of the New Seven Wonders of Nature, known for its dramatic flat summit and sweeping panoramic views over the Atlantic and city below.

In the afternoon, explore the vibrant neighborhood of Bo-Kaap, famous for its vividly painted homes and rich Cape Malay heritage—one of the most visually striking areas in Cape Town.

Lunch at Bo-Kaap Kombuis – A beloved local spot offering traditional Cape Malay cuisine with sweeping city views.

In the evening:

Dinner at a hyper-seasonal, seafood-focused restaurant that celebrates South Africa’s coastline in a refined yet relaxed way. Drinks at one of Jaco’s favorite bars – A hidden speakeasy that feels like stepping into a secret 1920s world, where every detail is theatrical, immersive, and just a little bit mysterious.

Day 3 - Sep 8: Markets & Constantia Valley

Start your morning at the lively Oranjezicht City Farm Market, known for its beautifully curated stalls, local produce, and relaxed, design-conscious crowd.

Take a private bus to continue to Groot Constantia, South Africa’s oldest wine estate, where Cape Dutch architecture, history, and wine culture come together in a uniquely atmospheric setting.

Lunch at La Colombe – Consistently ranked among the best restaurants in the world, offering an artful, multi-sensory dining experience set in the lush Constantia Valley.Enjoy a late dinner on your own back at the waterfront or in the city.

Day 4 - Sep 9: Cape Peninsula, Chapman’s Peak & Penguins

Set out on a full-day Cape Peninsula tour, one of the most breathtaking coastal routes in the world. Drive along Chapman’s Peak Drive, a winding cliffside road carved into the mountains, with dramatic ocean views that feel almost cinematic.

Continue on to:

Cape Point Lighthouse – Perched at the edge of the continent, where rugged cliffs meet the open ocean. Lunch set right above the ocean, in one of the most spectacular dining locations in Cape Town, known for its inventive small plates and unforgettable views of the beach – Home to a protected colony of African penguins, offering a rare chance to see them up close in their natural habitat. Enjoy a late dinner on your own back at the waterfront or in the city.

Day 5 - Sep 10: Open Day + Group Evening

Enjoy a flexible day to experience Cape Town at your own pace, with a curated list of local recommendations for shopping, eating and exploring.

Regroup in the evening:

Sunset cocktails at The Gin Bar – A tucked-away courtyard bar specializing in botanical, locally inspired cocktails. Dinner a vibrant, share-style Indian dining experience that’s energetic, flavorful, and perfect for a group setting.

Days 6–8: Safari in Hoedspruit (2 Nights)

Day 6 - Sep 11: Into the Bush

Fly and transfer to the lodge. After settling in, head out on your first sunset game drive, when the bush begins to come alive and wildlife is most active.

Dinner will be served in a traditional boma setting, creating an immersive introduction to safari culture under the stars.

Day 7 - Sep 12: The Big Five

Depart early for a guided game drive through Kruger National Park, one of the most extraordinary wildlife reserves on earth: vast, untamed, and teeming with life, where each moment feels cinematic and every sighting, from a distant elephant herd to a resting lion, feels genuinely rare and thrilling.

Return to the lodge for rest and relaxation before dinner.

Day 8: Return to Cape Town

Transfer to Hoedspruit Airport for your flight back to Cape Town, continuing onward to the Winelands.

Days 8–11: The Winelands (3 Nights)

Day 8 - Sep 13: Stellenbosch Arrival

40 miles from Cape Town, arrive at a beautiful wine farm and spend the afternoon enjoying the farm’s offerings such as wine tastings, curated art, and peaceful open spaces.

Later, explore the town of Stellenbosch, known for its oak-lined streets and Cape Dutch architecture.

Walk to dinner at a stylish, intimate dining space offering globally inspired small plates that feel both creative and approachable.

Day 9 - Sep 14: Franschhoek & Wine Route Day

Begin your morning early at a charming café set on a working farm, perfect for a slow start with excellent coffee and pastries.

Explore Franschhoek on foot, a picturesque village known for its French heritage, boutique shops, and art galleries.

After exploring the town, the group with stop at:

La Motte Wine Estate – Known for its refined wines and beautifully curated tasting experiences, enjoy wine tasting and cheese plattersBoschendal – A historic estate with sprawling lawns, ideal for a relaxed picnic and wandering the grounds.

In the evening:

Dinner at an intimate Japanese fine dining experience set within one of the most visually stunning wine estates in the region.

Day 10 - Sep 15: Babylonstoren & Private Braai

Visit Babylonstoren, one of the most iconic farm estates in South Africa, celebrated for its extraordinary gardens, design-forward spaces, and farm-to-table philosophy.

Enjoy breakfast in the greenhouse, wander through the gardens, and explore the farm shop.

Return to your wine farm for downtime before a special farewell evening:

A private braai (South African barbecue) prepared by Chef Jaco at a local farm—an intimate, authentic, and memorable final night.

Day 11 - Sep 16: Departure

Enjoy a relaxed breakfast at Spier before transferring to Cape Town International Airport for your onward journey home.

You have heard about Cape Town. Now experience it. In a VERY SPECIAL way that no one else has. Ever.

Join Chef Jaco Smith for an elevated, 11-day culinary journey that bridges the gap between South Africa’s vibrant urban energy and its untamed natural beauty. Starting in Cape Town, you’ll explore the historic Bo-Kaap neighborhood and dine at world-renowned spots, at while at your waterfront home base. From the dramatic heights of Table Mountain to the colony of African penguins at Boulders Beach, this first leg of the trip is a deep dive into the sensory richness of the Cape Peninsula.

The adventure then transitions into the wild heart of the country with a boutique safari experience at Safari Moon Luxury Bush Lodge. Here, you’ll trade city lights for the star-filled skies of Hoedspruit, tracking the Big Five in Kruger National Park and sharing stories over traditional boma dinners. The journey concludes in the serene Winelands, where days are spent wandering the historic gardens of Babylonstoren and sampling world-class vintages at Groot Constantia. It is a seamless blend of luxury, heritage, and flavor, culminating in an intimate, private braai prepared by Chef Jaco himself.

Jaco Smith, your chef host:

Jaco Smith was born and raised in a small town in South Africa, where his lifelong love for food began in his mother’s kitchen. His father was deeply involved in South African politics, and during the 1980s, members of parliament traveling between Johannesburg and Cape Town would often stay in their home. Important meetings were held around the family table, and Jaco’s mother cooked for visiting dignitaries—instilling in him an early understanding of how food brings people together.

As the demands on the household grew, Jaco’s mother hired a local African chef named Trudy from a nearby hotel. Trudy’s eyesight was failing, and she could no longer read recipes, but what she lacked in vision she made up for in heart and intuition. She quickly formed a special bond with young Jaco, eagerly waiting for him to return from kindergarten each day. With ingredients pre-measured and ready, she turned baking bread and cookies into moments of joy, creativity, and laughter—making the kitchen a place of magic.

Jaco continued learning alongside his mother, who patiently passed down her treasured recipes and techniques. As he grew older, so did his awareness of the country around him. His father became increasingly active in the fight against apartheid, joining the African National Congress and working toward the release of Nelson Mandela after 27 years of imprisonment.

“I will never forget watching my father speak at rallies of thousands—believing deeply in change and helping shape a new South Africa.”

That belief, pride, and sense of purpose continue to shape everything Jaco does today.

Pricing/Terms

11 days/10 nights

Price for bookings until 6/30/26: $10,950/pp Double Occupancy / $3000 single supplement (see deposit and payment details below)  After 6/30/26: $11,450/pp DO  All pricing guaranteed when booked. Website pricing may change due to cost factors.

Payments split into three parts: 30% of cost of trip due upon booking. 40% due by 12/31/2026. Then, balance of full cost of trip due by 5/30/27. All payments are non-refundable unless we notify you that we haven’t met the minimum number of guests by 5/15/2027. Payments made by check only. 

While our trips feature smaller groups for maximum enjoyment and interaction, this trip is subject to a low minimum number of guests. Please do not buy airfare until we inform you that the minimum has been met.

WHAT IS INCLUDED: This trip includes accommodations in beautiful 4-Star hotels and a boutique inn, hotel taxes, and experiences outlined on website (subject to minor changes) in addition to breakfast, and associated gratuities, and transportation to our excursions in the country away from the cities during the trip. All food and wine at the meals described on the website.

The flights to and from Hoedspruit will be included, in addition to transfers between locations and to the airport.

You do not have to worry about tips at restaurants, for bus drivers on our tour or guides.

WHAT ISN’T INCLUDED: Airfare or trip insurance (mandated for this trip) which can be purchased online or through an affiliation we have with Wanderwell, here. Hotel mini-bar, incidentals, food or wine not published on itinerary (or ordered separately). Tips for hotel personnel.

DIETARY RESTRICTIONS: This is called Portland Food ADVENTURES for a reason. Our trips are not great for people with restrictive food issues or preferences. Plus, on this trip, you will have the opportunity to try things you may not have ever had before. Pescatarians can generally be accommodated with advance notice.

MOBILITY: Also, you must be able to walk without issue and negotiate stairs.

Lastly, our groups are really fun, and we want to make sure we keep them that way. So, if you’re a flexible, open traveler who appreciates the opportunity to sit back and let us do the planning and the legwork while you eat and drink really well, this trip is for you. If you need to be in complete control of your schedule, and need to know what’s happening months in advance on Friday at 3pm during the trip, this may not be the best way for you to travel. Our guests who put this in our hands report the times of their lives!!

YOU ARE WELCOME AND ENCOURAGED TO CALL CHRIS AT 503 314 4221 TO DISCUSS THE TRIP BEFORE OR AFTER MAKING YOUR DEPOSIT.  THERE MAY BE SPECIAL OFFERS AVAILABLE ONLY OVER THE PHONE!!